


Dress Up

by HeathenVampires



Category: Supernatural
Genre: Brother/Brother Incest, Crossdressing, Double Anal Penetration, Explicit Sexual Content, Gay Sex, I forgot I even wrote Supernatural fics, Incest, M/M, Makeup, Makeup-Wearing Castiel (Supernatural), Makeup-Wearing Dean Winchester, Multi, Old School, Sibling Incest, flagrant disregard for the sanctity of trench coats, here share the pain, set like season 4 or 5 I think, this is really old and terrible
Language: English
Status: In-Progress
Published: 2019-03-04
Updated: 2019-03-03
Packaged: 2019-11-09 00:23:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,841
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17991356
Author URL: https://archiveofourown.org/users/HeathenVampires/pseuds/HeathenVampires
Summary: "You're all man Dean. I just want to see."





	Dress Up

**(I wrote this _forever_ ago and only just moved it to AO3) (so if its terrible sorry I literally wrote it in 2016 on a smartphone)**  


**Don't own the characters - just thoroughly corrupt them. Established Sam/Dean relationship.**

**Warnings for double penetration, cross dressing, wincest, group and all that fun stuff.**

**On we go!**

-SPN-

Dean may mock him for being "too tall", but Sam knew his brother loved his long, lean body. Especially at times like this, endless legs wrapped tight around Deans waist as he thrusted into Sam harder, faster, chasing the peak of pleasure they could only find in each other.

"Dean, _please."_

Sam didn't even know what he was begging for, tightening his muscular thighs around Dean and moving his hips in sync, desperately seeking release. His brother took pity on the writhing form, reaching a rough, calloused hand down to stroke Sam's cock, hypersensitive with the climax he could feel just out of reach.

"Come on baby brother, come for me."

The 'pet name' always had the same effect, pushing Sam to crest the wave before crashing over, coming on himself and arching as he groaned in pleasure. It was rare for one to come without the other following, and Sam whimpered slightly as Dean spurted, hot and thick as his cock swelled and twitched with orgasm. There was always an edge of discomfort as Dean pulled out, but warm and sated in his afterglow, Sam barely noticed as Dean dropped down heavily next to him.

"You just get better every time baby brother."

Sam was about to answer with something equally witty, but all that came out was a shriek of surprise as the motel room suddenly contained a slightly confused looking angel.

"Damnit Cas, do angels have no sense of privacy?"

Given that Cas was staring intently at their naked bodies without even indicating he had heard Dean, Sam doubted it.

"While I don't condemn any sexual orientation between consenting adults, I don't understand the goal. You two cannot produce offspring, though as you are related that would be unfavorable regardless. Why do humans mate if not for procreation?"

Dean grunted, tugging on boxer shorts and moving to the fridge for a beer - apparently unaware or uncaring of the ejaculate Sam had shot over his torso. Shuffling upright awkwardly, Sam bolted for the shower - Dean could give Cas the birds and bees talk since he was the one who had corrupted the angel to begin with. Team Free Will and all that. By the time he got out of a surprisingly hot shower - it was a kind of roulette in motels - Dean had given a vague, vulgar description that had Castiel looking a little more lost than usual.

"So it's not mating, it's sexual intercourse and it produces pleasurable sensations?"

"That's right Cas."

This was not a conversation Sam wanted to have with anyone, let alone an angel of heaven. Taking the beer Dean offered, Sam sat a little gingerly on the edge of his bed and drank deeply, trying to mask the mounting anxiety that Cas was about to freak out about two brothers having a lot of sex with each other. The expected freak out didn't come, a kind of intense silence filling the room for a few minutes.

"So if two male humans mate, sorry, have sexual intercourse, which one is the female equivalent?"

Smirking knowingly at Dean, Sam tried to correct Cas.

"Neither. If we wanted a female, we would find one. We are both all male in the relationship, regardless of who tops that night."

Dean was a little more crude, smiling in a way that was both open and seductive as he wiggled his eyebrows suggestively.

"I don't bang Sammy cus I can't get a girl, it's just so much better with a guy. Plus, he bangs me good and hard too."

Hoping Dean didn't shoot him, purely for the look of surprise on the angels face, Sam drained his beer and wiped his mouth before adding

"Dean likes to be a girl for me sometimes."

Castiel did indeed look perplexed, and Dean looked like he was seriously contemplating pulling his gun out in an entirely non-euphemistic way.

"Seriously Sammy? You gonna start shouting about that?"

Smiling unapologetically, Sam shrugged.

"He could have landed in here when you were wearing a pretty skirt and blowing me with that cute pink lip gloss on anyway."

"I don't understand. I thought neither of you were female."

"We aren't Cas, but some people like to play dress up. Dean happens to be one of them. Though he might shoot me now so I'll never see him sitting pretty again."

Cas looked between them, cocking his head and clearly trying to work something out.

"Can you show me? I think this is one of those things I require demonstration of."

"An angel of the Lord wants to watch me get fucked by my brother?"

"Is that something I shouldn't want?"

Chuckling at Castiels innocent eyes, Sam looked to Dean.

"I'm game if you are big brother."

"You know me. Always down to break the rules."

Sam could already feel his cock twitching in interest, Dean's boxers beginning to tent under the motel table.

"Better choose your outfit then."

Dean scowled, but there was a smirk at the edges so Sam reclined on the bed, his posture screaming "I'm waiting". Dean drained the last of his beer, standing up and nobody could have missed Cas looking at the rising erection with wide eyes.

"That's nothing angel, wait for the real show."

Cas swallowed heavily, no words leaving his slightly open mouth. If Sam didn't know better, he would say the angel was aroused. Shaking the thought away - it surely wasn't possible - he watched as Dean rooted through his duffel bag before disappearing into the singing through his nerves, Sam squeezed at his erection as he listened to Dean "getting ready". He knew all the sounds by now, the ping of elastic where Dean pulled on lace panties, the zipper where he did up the dress (finding one to fit for a 'bachelor party' had been fun), the sound of lip gloss and mascara being opened. The last sound, a click, confused him but he figured he would know when Dean came back out. Cas was watching the door himself, no doubt wondering what would come back out. The first time Dean had put makeup on was as a joke, letting one of the daughters of their various babysitters as teenagers "play" - an already seasoned hunter at the mercy of a nine year old girl had stayed with Sam forever. He had thought little more of it, going off to college and losing touch with the family.

_When Dean came back for him, pulling him into true Winchester life again, Sam had all but forgotten that time until he returned early from a girls house, liking her less and less as the alcohol he had drunk wore off. He still remembered Dean's yelp, bending down in the sink to scrub at his face - he hadn't even closed the bathroom door. Spotting the makeup tubes on the bathroom side, Sam put two and two together._

_"Dean, were you putting makeup on?"_

_"No! What on earth would I do that for?"_

_Sam had shrugged, popping open a beer and taking a long gulp._

_"I don't know, you might like it?"_

_Eventually, Dean admitted he did like it, but nobody was allowed to know because he didn't want to be a laughing stock, and their father would never understand. Nodding in agreement, Sam never brought it up again. Until their father had died, the mindless grief somehow ending in Sam and Dean falling into bed together, taking turns pounding out frustration and loss into each other until they were both bruised and drained and sore._

_They had avoided each other for a couple of hours, and Dean was halfway to alcohol poisoning by the time Sam returned to their motel room._

_"Sammy..."_

_Dean didn't get any further before bolting into the bathroom, throwing up and almost passing out. Used to this on occasion, Sam wiped his mouth and dumped Dean on his bed to sleep it off. They could talk in the morning. When Dean woke up, a hangover to add to his no doubt aching body (if Sam's was anything to go by, it still felt like Dean was inside him if he moved too fast) making pained groans leave his mouth, Sam made them both coffee and waited for Dean to join the land of the living._

_"Dean, we gotta talk."_

_"No we don't."_

_Voice rough with sleep and last nights drinking, Dean turned away from him._

_"I miss dad too. But I don't regret last night. If you do, I'm sorry."_

_There was silence broken only by Sam sipping his coffee and Dean noisily slurping his for a few minutes, then Dean's near inaudible whisper of "I don't either." Relief flooded Sam for a moment, glad one night of madness hadn't cost him his brother._

_They didn't talk about it much from then on, sex was just another part of their life as they went. Losing Dean to that demon deal had torn a hole in Sam, one he filled with demon blood and Ruby and darkness. The first chance they got was spent frantically reconnecting, and neither of them could walk straight the next day. If Bobby suspected something, he had never said. Then Castiel had come along, talking about seals and Lilith and Lucifer. The brothers fell out over Ruby, the demon blood and a hundred other things. It always resolved itself the same way, harsh and rough sex followed by drunken words of forgiveness. Along the lines somewhere, probably half down to whiskey, Sam had convinced Dean to put on makeup again. Dean was hesitant, saying he didn't want Sam seeing him as a girl._

_"You're all man Dean, I just want to see."_

_That night had probably been some of the best sex they had ever had, and it only got better as Dean let Sam push it further. It wasn't about Dean being "weak" or "inferior", he just looked hot as hellfire and Sam loved it. They had tried Sam in makeup and lace, but both admitted they preferred it on Dean._

Dragging himself away from nostalgic memories, the bathroom door opened. Dean stepped out, a black dress with a green shimmer in the light straining across the broad musculature of Dean's chest and shoulders. His perfect cheekbones and nose needed no help, but a light layer of mascara turned Dean's already sweeping, long eyelashes into works of art framing those perfect green eyes. Lip gloss enchanted his mouth, the near-pouting lips sparkling like a beacon Sam needed to answer. There was a faint glitter around his eyelids, just enough to draw a little more attention to his beautiful eyes.

"How's this Sammy?"

"Perfect. Come on then, Cas wanted a demonstration after all."

Dean slinked over to the bed, stradding Sam's hips and leaning down to kiss him. Hands slid under the dress, cupping Dean's ass and feeling the lace material. Dean's cock strained at the front, leaking when Sam wrapped a hand around the stiff length.

Truth be told, Sam would have forgotten Castiel was even there if he hadn't moved, sitting on the other bed to get a better view of the brothers. The angels pupils were dilated, tongue peeking out to lick chapped, dry lips though Sam didn't think he knew he was doing it. The brothers shared a smirk, silently agreeing to keep pushing the angel, to see how far he could go just watching. Resuming their kissing and groping, Sam could feel slick moisture between Dean's ass cleft.

"Oh, I'm all wet and ready for you baby brother."

Groaning and thrusting his hips upwards, Sam realised what the click he had heard was - lubricant.

"Fuck Dean, you're perfect you know that?"

Dean rolled his hips, grinding their erect cocks together and even through his jeans and Dean's layers, Sam groaned at the feeling. Hands tugged at his zipper, fumbling and rearranging limbs to get the denim down and out of their way. The impeding fabric gone, Sam's cock sprung up between them, pulsing to get inside Dean. There was a scramble for the tube of lube Dean always put in his bedside table in every motel, right next to the bible that almost every motel had. Sliding lubricated palms together over Sam's cock, he grunted at the teasing pleasure until Dean deemed him wet enough. The next fumbling was to push up the skirt of Dean's dress, separating just long enough to pull away the lacy underwear before Dean was straddling his lap again.

They shuddered simultaneously as Dean lowered himself, sinking down Sam's erection with relative ease until they were flush against each other. He let Dean set the rhythm, thrusting up as Dean dropped down and rubbing his thumb over Dean's shaft to stimulate him inside and out. Confusion sparked when Dean stopped, flicking eyes over at Cas. Sam raised an eyebrow to say "are you sure?" and Dean nodded, smirking darkly. Sam nodded in reponse, looking over and finding an unmistakable bulge tenting Castiels trousers.

"Hey, Cas. You want to get in on this?"

The angel jumped, as though he had forgotten they could even see him.

"I beg your pardon?"

"You. Sexual intercourse. Now. With us?"

Fighting not to just fuck into Dean with abandon as it was, there was an undeniable allure to them truly pushing Cas past normal angel limits. And the vessel he wore was not unattractive either, which certainly helped.

"I... I don't know how."

"Well for starters, lose the clothes."

Barely a second after Dean spoke, Cas was naked.  _Angels._ Slender, lean muscles and a respectably sized erection filled Sam's vision, though Cas didn't seem to understand.

"Now come kneel behind Dean, and get a handful of this on your cock."

Cas took the tube, kneeling behind Dean, and Sam had to bite back a laugh as Castiel jumped in surprise when he lubed his erection.

"Is it supposed to feel... Strange?"

"Its good, you'll get used to it. Now, line your cock up with Sammy here and push in. Slow and easy Cas, it's not rocket science."

Cas was hesitant but complied, and Sam made himself stay still, stroking Dean's cock just enough to distract from what must be wicked on the nerves as he was stretched wider.

"That's it angel boy, now stay like that for a minute."

Dean writhed between them, adjusting to the extra pressure. After a few minutes of Sam still rubbing at his erection, Dean nodded and rocked his hips.

"Now Cas, move your hips so you kind of pull out, but not all the way."

Dean had likely just taken an angel of heaven's virginity, but nobody seemed to notice as Cas followed instructions, the gravelly deep voice intoning grunts and groans as his body took over instinctively.

"He's got it Sammy, feel free to join in any time."

Thrusting up sharply for Dean's cheek, Sam did indeed join in, sliding up and down in opposition to Cas so Dean was torn between one or the other filling him, and the feel of a hard cock sliding against his own while inside Dean was frankly amazing, and Sam wished he hadn't wasted years of his life never knowing it. Now the initial pain of entry was fading, Dean was more active than either of them, rocking and bouncing between them for more stimulation.

"Come on you two, what's it take to get fucked properly round here?"

Castiel more than rose to the occasion, a faint white glow behind his eyes making Sam worry for a second but Dean was practically coming on the spot as the angel let loose, thrusting hard and fast into Dean until he spilled between their bodies, shaking all over and whimpering as Sam and Cas both thrusted up and came deep inside him.

"Wow, that was... Heavenly."

Dean couldn't resist making dumb puns when his voice came back, clearly. Castiel took a minute to clock on what he was supposed to do next, pulling out of Dean and stepping back.

"I am... Sticky."

"Join the club feathers, sex is meant to be good and messy."

Dean carefully lifted off Sam, hissing in pain and dropping down next to him in an ungainly, satisfied heap.

"You ok big brother?"

"Just a little roughed up, I can handle it. Your ass is mine next time though."

"Is it a Rota? Mandatory turn taking?"

"Not for everyone Cas, but with us it's pretty even."

"Does that mean I get to dress up?"

Sam and Dean looked at each other in surprise before sharing a grin.

"You can play dress up if you like Cas."

-SPN-

**I hope someone enjoys this hot mess I wrote years ago, I'll add the other 3 chapters at some point soon.  
**


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